1,1-Dichloroethane → HCID 86606925, compound
Reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@@H:16]2[C@@H:21]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C@H:20]([CH:29]=O)[CH2:19][CH2:18][O:17]2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl.C1[C:38]2(CCN[CH2:40][CH2:39]2)[CH2:37][CH2:36]O1.C([N:46]([CH2:49][CH3:50])CC)C.[C:51](O[BH-](OC(=O)C)OC(=O)C)(=[O:53])C.[Na+].ClC(Cl)C.C(=O)(O)[O-].[Na+]>>[F:32][C:2]([F:31])([F:1])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@@H:16]2[C@@H:21]([C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[C@H:20]([CH2:29][CH:38]3[CH2:39][CH2:40][C:50]4([CH2:51][O:53][NH:46][CH2:49]4)[CH2:36][CH2:37]3)[CH2:19][CH2:18][O:17]2)[CH3:14])[CH:6]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:8]=1Participants
7
Procedure
A mixture of 2-[1-{(2R,3R,4R)-2-[(1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy]-3-(4-fluorophenyl)-tetrahydropyran-4-carbaldehyde (Description 11; 0.15 g, 0.32 mmol), 2-oxa-8-azaspiro[4.5]decane hydrochloride (0.85 g, 0.48 mmol), triethylamine (50 μL, 0.49 mmol), sodium triacetoxyborohydride (0.136 g, 0.64 mmol) and dichloroethane (3 ml) was stirred at room temperature for 2 hours. The mixture was treated with sodium bicarbonate and extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on alumina (grade III) using ethyl acetate in hexane (10-50%) to give the title compound.
Workup
- extractionextracted into dichloromethane
- dry with materialThe combined organic extracts were dried (Na2SO4)
- concentrationconcentrated
- customThe residue was purified by chromatography on alumina (grade III)
Sources & evidence
- ORD record
- ord-9fc377742abb402c9980a21199564eef
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07393858B2
Reaction notes
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